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Upcoming Events

Embrace the allure of our Eastern Shore haven, where each passing season ushers in its own tapestry of charm and adventure! As we peer into the unfolding year, we're excited to present exciting happenings and unforgettable moments. Whether you're drawn to the vibrant hues of spring's awakening, the spirited festivities of summer's peak, the rustic warmth of autumn's embrace, or the magical enchantment of winter's frost, there's an experience tailored to enchant every soul. Navigate below to find the ideal time to plan your stay.


starry sky

An ASTROnomical Experience with Sky Guy Greg Redfern

Join us for an unforgettable astro experience June 9th and 10th where we'll unlock the secrets of the night sky with Sky Guy Greg Redfern! Discover how to capture stunning celestial moments with your camera and smartphone in our hands-on workshops. Dive into the heart of the cosmos with safe Sun viewing sessions, and as the night falls, immerse yourself in our under the stars star party, where constellations come alive. 

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25% off Two-Nights
35% off Three-Nights

Take a look at what Sky Guy Greg has to say in his blog – click here!

Sparkling Afternoons

Sparkling Afternoons

Dive into 'SPARKLING' Afternoons every Friday by the water (weather permitting)! From 3:00pm to 6:00pm, indulge in our Champagne Bar, groove to LIVE music, and savor bites from our Lite Bite Menu. Come early and soak up the fun!

Antique boat at dock

CBMM Antique & Classic Boat Festival and Coastal Arts Fair

Mark your calendars for June 14 - 16th as the Chesapeake Bay Maritime Museum comes to life with the 36th Antique & Classic Boat Festival. Pair these nautical spectacles with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat!

fireworks from a boat

Independence Day

Come celebrate Independence Day with us and experience the excitement of front-row seats to St. Michaels spectacular fireworks display on Saturday, July 6th! It's the perfect way to create lasting memories and honor the spirit of freedom in our picturesque town. Visit here to learn more!

easel with painting and paint

Plein Air Easton

Plein Air Easton, celebrating its 20th year July 12 - 21 2024, is the largest juried plein air painting competition in the U.S and a perfect excuse to plan a visit. Hosted by the Avalon Foundation in Easton, Maryland, each July, it draws talented artists from around the world. Learn more about Plein Air Easton by visiting here

Chesapeake Bay Maritime Museum

CBMM Waterman’s Appreciation Day & Crab Feast

Mark your calendars for August 11th as the Chesapeake Bay Maritime Museum comes to life with the Waterman’s Appreciation Day & Crab Feast. Pair these nautical spectacles with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat! Visit here to read about the history and importance of the Chesapeake Bay Watermen. 


theatre interior

Chesapeake Film Festival

The prestigious Chesapeake Film Festival returns to Easton, Maryland from September 27th to September 29th, 2024! Immerse yourself in the magic of cinema with a captivating lineup of acclaimed films, thought - provoking documentaries, and engaging discussions with industry experts.

Not So Scary Commodore Perry Scarecrow

Fall Into St. Michaels

Fall into the enchantment of St. Michaels during the third weekend in October! Experience the charm of our scenic town as it comes alive with scarecrow contests, pumpkin pie eating competitions, and pumpkin carving festivities scattered throughout. Immerse yourself in the vibrant spirit of the season as you wander the streets adorned with whimsical creations.

oysters on a plate

Oyster Fest

Get ready to indulge in the flavors of the Chesapeake Bay's favorite fall festival! Join us for Chesapeake Bay Maritime Museum’s Oyster Fest on Saturday, October 26th for a day filled with live music, exciting retriever demonstrations, and of course, mouthwatering oysters and more. Sip on local brews, slurp down freshly shucked oysters, and savor the taste of autumn by the bay. It's an event you won't want to miss!

ducks on a pond

Waterfowl Festival

Experience the charm of the Eastern Shore at Easton's Waterfowl Festival, taking place from November 8th to 10th, 2024! Delight in a weekend filled with exquisite art collections, culinary delights, and the authentic ambiance of the Chesapeake Bay. Immerse yourself in the rich tradition of waterfowl calling and witness captivating live demonstrations. Don't miss this true Eastern Shore classic, where art, culture, and nature converge for an unforgettable celebration!

santa dancing on the street

Lighting of the Lane

Join us for a cherished tradition at the Inn at Perry Cabin: the enchanting Lighting of the Lane! As the holiday season approaches, witness the magic unfold with the illumination of thousands of twinkling lights along Watkins Lane. Delight in the festive atmosphere with delectable lite bites, beverages to warm the soul, and the possibility of snowflakes dancing in the air. Experience the joy and wonder of the holidays as we come together to celebrate this magical moment, marking the beginning of a season filled with warmth, love, and cherished memories. More details to come... 


couple looking at pretty lights

Midnight Madness

Step into the magic of Midnight Madness the first weekend of December in St. Michaels. Our charming shops extend their hours, welcoming you with festive refreshments, delectable snacks, and exclusive sales. Every purchase at participating businesses brings you closer to winning delightful gift baskets, adding to the joy of the season.

the grinch in a boat in a parade

Christmas in St. Michaels

Experience the magic of Christmas in St. Michaels from December 13th to 15th! Join us for a weekend filled with joyous celebrations as our picturesque town comes alive with holiday spirit. Don't miss the enchanting Talbot Street Christmas Parade and the dazzling Lighted Boat Parade, where the waterfront sparkles with festive cheer. Throughout the town, discover a plethora of merry festivities to delight in with loved ones amidst the festive atmosphere of Christmas in St. Michaels.